β-Cyclodextrins influence on E-3,5,4′-trimethoxystilbene absorption across biological membrane model: A differential scanning calorimetry evidence

International Journal of Pharmaceutics

Volumn 388, Issue 1-2, 2010, Pages 144-150

  Sarpietro, Maria Grazia ^a   Ottimo, Sara ^a   Giuffrida, Maria Chiara ^a   Spatafora, Carmela ^a   Tringali, Corrado ^a   Castelli, Francesco ^a  

^a UNIVERSITY OF CATANIA   (Italy)

Author keywords

Cyclodextrins; 3,5,4 Trimethoxy trans stilbene; Biomembrane model; Differential scanning calorimetry; Dimyristoylphosphatidylcholine

Indexed keywords

3,5,4' TRIMETHOXYSTILBENE; BETA CYCLODEXTRIN DERIVATIVE; RESVERATROL; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CELL MEMBRANE PERMEABILITY; COMPLEX FORMATION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG ABSORPTION; DRUG SOLUBILITY; DRUG STRUCTURE; LIPOPHILICITY; MEMBRANE VESICLE; PRIORITY JOURNAL;

ANTINEOPLASTIC AGENTS; BETA-CYCLODEXTRINS; CALORIMETRY, DIFFERENTIAL SCANNING; CELL MEMBRANE; DIMYRISTOYLPHOSPHATIDYLCHOLINE; PERMEABILITY; SOLUBILITY; STILBENES;

EID: 76549114923     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2009.12.048     Document Type: Article

References (33)

1. Bach, D., 1984. Calorimetric studies of model and natural biomembranes. In: Chapman, D. (Ed.), Biomembrane Structure and Function; MacMillan: London, pp. 1-41.
2. Bader Y., Madelener S., Strasser S., Maier S., Saiko P., Stark N., Popescu R., Huber D., Gollinger M., Erker T., Handler N., Szakmary A., Jäger W., Kopp B., Tentes I., Fritzer-Szekeres M., Krupitza G., and Szekeres T. Stilbene analogues affect cell cycle progression and apoptosis independently of each other in an MCF-7 array of clones with distinct genetic and chemoresistant backgrounds. Oncol. Rep. 19 (2008) 801-810
3. Belleri M., Ribatti D., Nicoli S., Cotelli F., Forti L., Vannini V., Stivala L.A., and Presta M. Antiangiogenic and vascular-targeting activity of the microtubule-destabilizing trans-resveratrol derivative 3,5,4′-trimethoxystilbene. Mol. Pharmacol. 67 (2005) 1451-1459
4. Blair G.E., Cassady J.M., Robbers J.E., Tyler V.E., and Raffauf R.F. Isolation of 3,4′,5-trimethoxy-trans-stilbene, otobaene and hydroxyotobain from Virola cuspidata. Phytochemistry 8 (1969) 497-500
5. Castelli F., Caruso S., and Giuffrida N. Different effect of two structurally similar carotenoids, lutein and β-carotene, on the thermotropic behavior of phosphatidylcholine liposomes. Calorimetric evidence of their hindered transport trough biomembranes. Thermochim. Acta 327 (1999) 125-131
6. Castelli F., Uccella N., Saija A., and Trombetta D. Differences between coumaric and cinnamic acids in membrane permeation as evidenced by time-dependent calorimetry. J. Agric. Food Chem. 47 (1999) 991-995
7. Castelli F., Giuffrida N., Tringali C., and Ruberto G. Calorimetric evidence of differentiate transport of limonin and nomilin through biomembranes. J. Agric. Food Chem. 48 (2000) 4123-4127
8. Del Valle E.M.M. Cyclodextrins and their uses: a review. Process Biochem. 39 (2004) 1033-1046
9. Gardikis K., Hatziantoniou S., Viras K., Wagner M., and Demetzos C. A DSC and Raman spectroscopy study on the effect of PAMAM dendrimer on DPPC model lipid membranes. Int. J. Pharm. 318 (2006) 118-123
10. Huang C., and Li S. Calorimetric and molecular mechanics studies of the thermotropic phase behavior of membrane phospholipids. Biochim. Biophys. Acta 1422 (1999) 273-307
11. Karathanos V.T., Mourtzinos I., Yannakopoulou K., and Andrikopoulos N.K. Study of the solubility, antioxidant activity and structure of inclusion complex of vanillin with β-cyclodextrin. Food Chem. 101 (2007) 652-658
12. Lançon A., Henet N., Jannen B., Delmas D., Heyuel J.-M., Lizard G., Chagnot M.-C., Artur Y., and Latruffe N. Resveratrol in human hepatoma HepG2 cells: metabolism and inducibility of detoxifying enzymes. Drug Metab. Dispos. 35 (2007) 699-703
13. Lesieur S., Charon D., Lesieur P., Ringard-Lefebvure C., Muguet V., Duchêne D., and Wouessidjewe D. Phase behavior of fully hydrated DMPC-amphiphilic cyclodextrin systems. Chem. Phys. Lipids 106 (2000) 127-144
14. Lin H.-S., and Ho P.C. A rapid HPLC method for the quantification of 3,5,4′-trimethoxy-trans-stilbene (TMS) in rat plasma and its application in pharmacokinetic study. J. Pharm. Biomed. Anal. 49 (2009) 387-392
15. Loftsson T., Hreinsdottir D., and Masson M. Evaluation of cyclodextrin solubilization of drugs. Int. J. Pharm. 302 (2005) 18-28
16. Lu Z., Cheng B., Hu Y., Zhang Y., and Zou G. Complexation of resveratrol with cyclodextrins: Solubility and antioxidant activity. Food Chem. 113 (2009) 17-20
17. Mabrey-Gaud S. Differential scanning calorimetry of liposomes. In: Knight C.G. (Ed). Liposomes: From Physical Structure to Therapeutic Applications (1981), Elsevier/North-Holland, Amsterdam 105-138
18. MacRae W.D., and Towers G.H.N. Nonalkaloidal constituents of Virola elongata bark. Phytochemistry 24 (1985) 561-566
19. Marsh D. Physical characterization of liposomes for understanding structure-function relationships in biological membranes. In: Barenholz Y., and Lasic D.D. (Eds). Handbook of Nonmedical Applications of Liposome (1996), CRC Press, Boca Raton, FL 21-49
20. Másson M., Loftsson T., Jónsdóttir S., Fridriksdóttir H., and Petersen D.S. Stabilisation of ionic drugs through complexation with non-ionic and ionic cyclodextrins. Int. J. Pharm. 164 (1998) 45-55
21. Pan M.H., Gao J.H., Lai C.S., Wang Y.J., Chen W.M., Lo C.Y., Wang M., Dushenkov S., and Ho C.T. Antitumor activity of 3,5,4′-trimethoxystilbene in COLO 205 cells and xenografts in SCID mice. Mol. Carcinog. 47 (2008) 184-196
22. Redenti E., Szente L., and Szejtli J. Cyclodextrin complexes of salts of acidic drugs. Thermodynamic properties, structural features, and pharmaceutical applications. J. Pharm. Sci. 90 (2001) 979-986
23. Rouser G., Fkeischer S., and Yamamoto A. Two dimensional thin layer chromatographic separation of polar lipids and determination of phospholipids by phosphorus analysis of spots. Lipids 5 (1970) 494-496
24. Sarpietro M.G., Caruso S., Librando V., and Castelli F. Structure influence on biophenols solubility in model biomembranes detected by differential scanning calorimetry. Mol. Nutr. Food Res. 49 (2005) 944-949
25. Sarpietro M.G., Spatafora C., Tringali C., Micieli D., and Castelli F. Interaction of resveratrol and its trimethyl and triacetyl derivatives with biomembrane models studied by differential scanning calorimetry. J. Agric. Food Chem. 55 (2007) 3720-3728
26. Shimpi S., Chauhan B., and Shimpi P. Cyclodextrins: application in many routes of drug administration. Acta Pharm. 55 (2005) 139-156
27. Silvius J.R. Thermotropic properties of phospholipid analogues. Chem. Phys. Lipids 57 (1991) 241-252
28. Singh M., Sharma R., and Banerjee U.C. Biotechnological applications of cyclodextrins. Biotechnol. Adv. 20 (2002) 341-359
29. Spatafora C., Basini G., Baioni L., Grasselli F., Sofia A., and Tringali C. Antiangiogenic resveratrol analogues by mild m-cpba aromatic hydroxylation of 3,5-dimethoxystilbenes. Nat. Product Commun. 4 (2009) 239-246
30. Szejtli J., Bolla-Pusztai E., Szabo P., and Ferenczy T. Enhancement of stability and biological effect of cholecalciferol by α-cyclodextrin complexation. Pharmazie 35 (1980) 779-787
31. Szejtli J. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98 (1998) 1743-1753
32. Uekama K. Pharmaceutical application of cyclodextrins as multifunctional drug carriers. Yakugaku Zasski 124 (2004) 909-935
33. Walde P. Preparation of vesicles (liposomes). In: Nalwa H.S. (Ed). ASP Encyclopedia of Nanoscience and Nanotechnology vol. 9 (2004), American Scientific Publishers, Stevenson Ranch, CA 43-79